64641-81-2Relevant academic research and scientific papers
Strecker-type reaction of nitrones using cyanohydrin
Sakai, Takahiro,Soeta, Takahiro,Inomata, Katsuhiko,Ukaji, Yutaka
scheme or table, p. 231 - 235 (2012/04/23)
Strecker-type reaction of nitrones using acetone cyanohydrin as a cyanide source was developed. By treating nitrones with acetone cyanohydrin in the presence of n-BuMgCl, transcyanation from the cyanohydrin to the nitrones smoothly proceeded in THF at 35 °C. The amount of n-BuMgCl could be reduced to 0.2 equiv to give the corresponding α-cyanohydroxylamines in up to 98% yields.
Catalyst-free Strecker reaction in water: A simple and efficient protocol using acetone cyanohydrin as cyanide source
Galletti, Paola,Pori, Matteo,Giacomini, Daria
experimental part, p. 3896 - 3903 (2011/09/12)
A simple, convenient, and practical method for the synthesis of α-amino nitriles through a one-pot, three-component Strecker reaction of a carbonyl compound, amine, and acetone cyanohydrin in water has been developed. Reactions proceed very efficiently without any catalyst at room temperature with high chemoselectivity and give, in some cases, the expected α-amino nitrile pure after direct separation from water. The protocol is particularly efficient for both aliphatic and aromatic aldehydes, and cyclic ketones, in combination with primary and secondary amines. An unusual application of the Strecker reaction to 1,2-diamines to obtain 1,2-diamino nitriles, and to cyclic secondary amines is reported. Copyright
α-Phenylglycinol as chiral auxiliary in diastereoselective Strecker synthesis of α-amino acids
Chakraborty,Azhar Hussain,Venkat Reddy
, p. 9179 - 9190 (2007/10/02)
The high diastereoselectivity achieved in Strecker synthesis using inexpensive α-phenylglycinol as chiral auxiliary and its facile removal by oxidative clearange make it an ideal choice for the large scale preparations of optically active α-amino acids specially α-arylglycines present abundantly in glycopeptide antibiotics. A number of chiral amino acids are synthesized following this method. Also molecular mechanics calculations are carried out to explain the observed diastereoselection.
Diastereoselective Strecker Synthesis using α-Phenylglycinol as Chiral Auxiliary
Chakraborty, T. K.,Reddy, G. V.,Hussain, K. Azhar
, p. 7597 - 7600 (2007/10/02)
Use of α-phenylglycinol as chiral auxiliary in Strecker synthesis ensures high diastereoselectivity and its easy removal by oxidative cleavage allows large scale preparation of optically active α-amino acids.
